2-Fluorobenzothiazole → Ethyl N-(2-benzothiazolyl)-O-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-L-tyrosinate

HRID 1759693Notes

Reaction equation

HRID 1759693 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][C@@H:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH2:21])=[CH:17][CH:16]=1.F[C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1>N1C=CC=CC=1>[S:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=[C:30]1[NH:21][C@H:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][NH:9][C:10]=3[N:1]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 707532-FluorobenzothiazoleHCID 69880410Ethyl O-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-L-tyrosinate

Product 1

HCID 86594969Ethyl N-(2-benzothiazolyl)-O-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-L-tyrosinate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture constituted by 1-4 (150 mg, 0.4 mmole) and 2-fluorobenzothiazole (75 mg; 0.5 mmole) in 3 ml of pyridine is agitated at ambient temperature then heated under reflux for minutes, followed by evaporating under reduced pressure and purifying by chromatography eluting with an AcOEt/CH2Cl2 mixture 50/50 in order to obtain 90 mg of the expected 2-1.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for minutes
  3. customby evaporating under reduced pressure
  4. custompurifying by chromatography
  5. washeluting with an AcOEt/CH2Cl2 mixture 50/50 in order
  6. customto obtain 90 mg of the

Sources & evidence

ORD record
ord-5858c0b315264f82a23d0ba4caaea6b9
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

Loading…